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How to Send Emails with Telnet 

Ketevan Bostoganashvili
This is a cover image for an article that explains How to Send Emails with Telnet

Telnet or Teletype Network Protocol is a client/server application protocol. It allows users to connect with the email servers directly from the command line of their computer. 

The primary purpose of Telnet is to establish a standardized connection between terminal-oriented devices and processes (RFC 854).

It could also be used for sending emails and, in that process, testing the Simple Mail Transfer Protocol (SMTP) connection. However, there are specific limitations preventing you from actually sending emails on production, and we’ll discuss them in detail.

Let’s move on to explain how to send emails using Telnet on Windows and Linux operating systems. 

Send emails via Telnet on Windows 

Prerequisites 

Installing the Telnet client 

Most versions of Windows operating systems don’t have Telnet enabled by default. So, to get started, first, we need to install the Telnet client. The installation process will differ slightly depending on the Windows version you’re using. Generally, we have three main options: 

Installation using the command line 

Press the Windows key or click the Start button. Locate the Start Search box, type cmd, and hit Enter. Right-click on the Command Prompt and press Run as administrator. That way, you’ll have the right to complete the installation. The next step is to dial in a specific command in the command line.

For Windows 7, Windows Server 2008 R2, Windows Server 2008, or Windows Vista, type in the following command and press Enter: 

pkgmgr /iu:"TelnetClient"

For Windows 8 and above, type in this command and press Enter: 

dism /online /Enable-Feature /FeatureName:TelnetClient

Wait for the installation to be completed. You should receive a confirmation message on newer versions of Windows OS. 

Installation using PowerShell 

Another option is to use PowerShell to install the Telnet client. However, it’s only applicable to Windows 8.1, Windows 10, Windows Server 2012 R2, or later. 

Open the PowerShell administrator window, type the following command, and press Enter. 

Enable-WindowsOptionalFeature -Online -FeatureName TelnetClient

Wait for the installation to be completed. 

Installation using Control Panel 

Finally, you can install the Telnet client from the Control Panel. To do so, find Programs (or Programs and Features) and open it. Locate Turn Windows features on or off and click on it. You’ll see a Windows Features box. Find Telnet Client and mark the checkbox. Then press OK. Wait for the installation to be completed and restart the computer to apply the changes. 

For other installation options, refer to the Microsoft documentation. 

Sending the emails 

The email-sending process follows the logic and order of SMTP transmission: handshake, transmission, and termination of the session. It uses SMTP commands and connects to the server through a TCP port. Check out this blog post to find more information on SMTP operation. 

Note: Telnet isn’t a secure way to send an email. It establishes an unencrypted connection, as it doesn’t support SSL or TLS. This means that anyone with access to your network can hijack the transmission and access the contents of your message. 

You can’t connect to SMTP servers with authentication either, as most of them require TLS or SSL encryption before allowing LOGIN and PLAIN authentication methods (authentication without TLS is allowed only on test SMTP servers). You should use OpenSSL instead of Telnet to connect to SMTP servers with encryption. We’ll be talking about OpenSSL below. 

Due to all that, we’ll actually cover “email sending” to Mailtrap sandbox which is a fake SMTP used for testing purposes.

To start an SMTP session, you’ll need the full domain name or the IP address of the SMTP server you’re trying to connect to. As said, we’ll use Mailtrap Email Testing, and enter: sandbox.smtp.mailtrap.io. 

You’ll also need to identify the port, which can be 25, 587, 465, or 2525. The port number depends on the configurations of the SMTP server you’re trying to connect to. Most SMTP servers block transmissions through port 25. Port 465 is suitable when sending emails with SSL encryption, while port 587 and 2525 should be used with TLS encryption. 

Type the command: 

telnet sandbox.smtp.mailtrap.io 2525

Note: Mailtrap Email Testing won’t accept Telnet connections through port 25. You’ll need to use port 2525. 

You’ll see the response starting with code 220 if the connection is successful. For example, 

220 sandbox.smtp.mailtrap.io ESMTP server ready

The next step is to identify yourself to the SMTP host. 

EHLO example.com or HELO example.com

Note: The HELO command will initiate an SMTP connection without service extensions. Therefore, corresponding ESMTP commands (such as STARTTLS, for example) won’t be supported. 

All the supported SMTP extensions will be listed in the response. Each line will start with 250, indicating a successful connection. 

250-sandbox.smtp.mailtrap.io
250-PIPELINING
250-SIZE 10485760
250-ETRN
250-STARTTLS
250-AUTH LOGIN PLAIN
250-ENHANCEDSTATUSCODES
250-8BITMIME
250 DSN

Then you can go ahead and transfer the necessary email fields according to the SMTP specification. First, type MAIL FROM, then RCPT TO, and then type DATA.

MAIL FROM: <sender@example.com>
250 2.1.0 Sender OK
RCPT TO: <recipient@example.com> 
250 2.1.5 Recipient OK
DATA
354 Start mail input; end with <CRLF>.<CRLF>
From: sender@example.com
To: recipient@example.com
Subject: Telnet email

This is my first test message sent using the Telnet client on Windows
.
250 2.0.0 Ok: queued as ABC123456789

To end the session, you should type the QUIT command. The server will respond with 221 2.0.0 Service closing transmission channel, and the connection will be terminated. 

A complete sample will look something like this: 

telnet sandbox.smtp.mailtrap.io 2525
220 sandbox.smtp.mailtrap.io ESMTP server ready
EHLO example.com
250-sandbox.smtp.mailtrap.io Hello
250-SIZE 37748736
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-STARTTLS
250-X-ANONYMOUSTLS
250-AUTH NTLM
250-X-EXPS GSSAPI NTLM
250-8BITMIME
250-BINARYMIME
250-CHUNKING
250 XRDST
MAIL FROM: <sender@example.com>
250 2.1.0 Sender OK
RCPT TO: <recipient@example.com>
250 2.1.5 Recipient OK
DATA
354 Start mail input; end with <CRLF>.<CRLF>
From: sender@example.com
To: recipient@example.com
Subject: Telnet email

This is my first test message sent using the Telnet client on Windows
.
250 2.0.0 Ok: queued as ABC123456789
QUIT
221 2.0.0 Service closing transmission channel

To learn how to send testing emails with Telnet on Windows, watch our dedicated tutorial:

Send emails using Telnet on Linux 

Sending emails using Telnet on a Linux console is mostly similar to Windows. The difference is in the installation process only. 

Prerequisites 

Installing the Telnet client 

If the Telnet client isn’t installed on your machine, you can install it from your package manager. Specific commands will differ depending on the Linux distribution you’re using. 

For Arch Linux and Manjaro, type in the following command in the terminal window and press Enter: 

$ sudo pacman -S inetutils

For Ubuntu, Kali Linux, Debian, and Linux Mint: 

$ sudo apt install telnet

For Red Hat, Fedora, and Centos: 

$ sudo dnf install telnet

You’ll be prompted to enter your administrator password. Type it in and press Enter once again. Wait for the installation to be completed. 

Sending the emails 

To start sending emails (again we’ll send to Mailtrap Email Testing sandbox), start the Telnet session by typing this command: 

$ telnet sandbox.smtp.mailtrap.io 25

Then proceed the same way we described above. Don’t forget to follow the exact order of SMTP commands, otherwise, the transmission won’t be successful. If you misspell any of the commands, you won’t be able to make corrections with backspace. It’s recommended to press Enter, wait for the error message, and send a correct command afterward. 

Send email messages with HTML body and attachments to multiple recipients 

It’s also possible to send HTML emails with Telnet. For that, you’ll need to define the Content-Type as text/html or multipart/alternative. This portion should be inserted into your email after the DATA command. 

DATA

Mime-Version: 1.0      
Content-Type: multipart/alternative; boundary="peaches"; 

--peaches
Content-Type: text/plain

This is a plain text message sent using Telnet

--peaches
Content-Type: text/html

<h1>This is an HTML message sent using Telnet</h1>

--peaches--
.
250 2.0.0 Ok: queued as ABC123456789
QUIT
221 2.0.0 Service closing transmission channel

Now let’s send an email with an attachment. To complete that task, we’ll need to format the message with MIME. The Content-Type should be defined as multipart/mixed to let the email server know that the email will contain multiple parts, including an attachment. The Content-Disposition header will include the attachment itself. 

DATA

From: sender@example.com
To: recipient@example.com
Subject: Telnet email with attachments

MIME-Version: 1.0
Content-Type: multipart/mixed; boundary=boundary_9876

--boundary_9876
Content-Type: text/plain

This is the email message body.

--boundary_9876
Content-Type: application/octet-stream
Content-Disposition: attachment; filename="mylovelycat.jpg"

This is the content of the attachment.

--boundary_9876--
.
QUIT

Finally, let’s send emails to multiple recipients. That’s the easiest part of all. We just need to send RCPT TO command several times and include the recipients’ addresses in the to field after the DATA command. For example: 

MAIL FROM: <sender@example.com>
250 2.1.0 Sender OK
RCPT TO: <recipient1@example.com>
250 2.1.5 Recipient OK
RCPT TO: <recipient2@example.com>
250 2.1.5 Recipient OK
RCPT TO: <recipient3@example.com>
250 2.1.5 Recipient OK
DATA
354 Start mail input; end with <CRLF>.<CRLF>
From: sender@example.com
To: recipient@example.com, recipient2@example.com, recipient3@example.com
Subject: Telnet email to multiple recipients

Can you send emails with Telnet using free SMTP servers? 

Yes and no. 

You won’t be able to send emails with the Telnet console to free SMTP servers using port 25. As mentioned above, it’s blocked by the majority of email clients. So, if you were to send an email to Gmail, Yahoo, or Microsoft Outlook, you’d need to use port 587.

Even so, the connection can only be used to test a specific port or a portion of the connection. Telnet doesn’t support SSL or TLS encryption, so the chances are you won’t be able to send emails successfully. We weren’t able to send emails by connecting to Gmail, Outlook, and Yahoo SMTP servers. 

To test the connection on different ports, you can just use telnet smtp.gmail.com 587, telnet smtp-mail.outlook.com 587, or telnet smtp.mail.yahoo.com 465 commands. If the response is 220, it indicates that there’s no issue with the given ports. 

Troubleshooting common Telnet errors 

When something goes wrong in your SMTP session, you’ll receive error messages. By interpreting them, you’ll be able to understand what’s the problem with the connection or the SMTP server. 

Here’s a list of the most common errors and how to fix them: 

Is there an alternative to sending emails using Telnet? 

As we mentioned above, Telnet is a non-secure way to send emails. Even if your chosen SMTP server allows you to use SMTP AUTH without SSL/TLS (most likely, none of the live SMTP servers will allow you to do so), your credentials will still be visible to anyone connected to the same network. 

Plus, your credentials will be encrypted with Base64 only, which is quite simple to decipher. That will leave you vulnerable to attacks. If your credentials are compromised, it will be easy for the attackers to send spoof emails or read the contents of your email messages. 

Moreover, to use the SMTP AUTH command on Windows, you need basic authentication. Unfortunately, Microsoft has deprecated basic authentication for new tenants, which means you won’t be able to undergo SMTP authentication from newer versions of Windows. This will force you to complete the session without SMTP AUTH. 

That’s why Telnet is usually used to send test emails, debug SMTP connections, or check if the SMTP server or Exchange Server is accessible through port 25. You should never use Telnet to send emails in production. And even if you just want to test email servers, there are better alternatives on the market, such as OpenSSL and Mailtrap. 

OpenSSL – Telnet alternative for encrypted email sending 

OpenSSL is an open-source command-line tool that supports SSL/TLS encryption. For installation instructions on Windows, Linux, and other operating systems, check out the official documentation. On Windows, you can also download the installer. On Linux, you can use base repositories and install OpenSSL using the following commands: 

Once the installation is completed, use the line below to connect to the SMTP server: 

openssl.exe s_client -starttls smtp -connect sandbox.smtp.mailtrap.io:25

Then you can greet the server and identify yourself with EHLO as we did with Telnet. Follow it up with the STARTTLS command and authenticate yourself using AUTH LOGIN or AUTH PLAIN commands. 

OpenSSL can be used for both staging and production environments. However, OpenSSL isn’t recommended for sending high volumes of emails. 

Mailtrap – Telnet alternative for testing and sending large volumes of emails 

Mailtrap is one platform to test, send, and control the performance of your infrastructure. It has two solutions: Email Testing and Email Sending. 

Mailtrap Email Testing is an Email Sandbox that enables you to safely inspect your emails in staging without spamming recipients. 

With Email Testing, you can test an SMTP relay or SMTP server by sending an email to a virtual inbox. You’ll just need to enter the Inbox Email Address as your recipient and easily troubleshoot sending issues. 

On top, Email Testing provides the credentials of the fake SMTP server, allowing you to easily integrate it with your app. For more flexibility and automated testing, you can use SDKs or ready-made code snippets.

Once Email Testing is integrated, you’ll be able to check HTML/CSS, preview your emails, check the tech info to validate headers, and inspect the spam score. All of this is available without the security issues Telnet has. 

When all the tests are completed, you can send high volumes of emails in production with Mailtrap Email Sending – an infrastructure with high deliverability rates by design. It can be integrated with your app using SMTP service or RESTful API, allowing for an easy and smooth setup. 

After sending the emails, you can monitor their performance with Email Sending’s Actionable Analytics feature. You can track essential email metrics or troubleshoot any unexpected sending issues if they occur. 

Try Mailtrap for Free

Wrapping up 

That’s it! Now you know how to send emails using Telnet from Windows and Linux. You can send simple email messages or add an HTML body, and even attachments. 

Remember, you should avoid sending emails using Telnet on production to prevent security issues and vulnerabilities. Using other tools such as Mailtrap Email Delivery Platform is much more reasonable. If you enjoy our tutorials, check out our guides on sending emails with PowerShell or sending emails with SMTP.

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